News and features writer

At ease: Lieutenant Colonel Cate McGregor is comfortable in her skin. Below, as Malcolm.

Lieutenant Colonel Cate McGregor is describing her first encounters with Tony Abbott in the early 1980s – on the rugby field and at a bar at Sydney University where the young leftie and the ‘‘coming man’’ of the right locked horns in a testosterone-fuelled game of one-upmanship.

‘‘We were taking a rise out of one another, niggling one another politically,’’ McGregor recalls. ‘‘And I really thought, ‘This guy’s such a schmuck. He’ll want a fight.’ I was goading him and he was goading me. But I soon discovered he was just a really good-natured bloke.’’

She and Abbott have been great mates ever since. Back then, though, she was he. She was Malcolm McGregor, the boy from Toowoomba, cricketer, rugby player, Duntroon graduate, precocious political warrior and a coming man of the Australian Labor Party. Malcolm had no inkling then that, in his mid-50s, he would be overwhelmed by a seismic and agonising realisation: ‘‘That unless I lived as a woman it would be futile going on.’’

The boy from Toowoomba: Malcolm McGregor.

On Monday night, Prime Minister Abbott introduced ABC television’s Australian Story and its feature on the remarkable life of Cate McGregor, AM.

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‘‘Tony has never allowed ideology to filter his friendships,’’ McGregor tells Fairfax Media over lunch in Sydney. Nor did Abbott’s social conservatism become a filter when McGregor, the speechwriter for Chief of Army David Morrison, decided to transition to womanhood in 2012.

Malcolm McGregor had worked as an adviser to NSW Labor leader Bob Carr before becoming a Labor ‘‘rat’’ and walking out of the party in the early 1990s. He then worked for federal Liberal leader John Hewson, as did Abbott, before blowing up his bridges there, too, with columns attacking the Libs in The Australian Financial Review.

‘‘I wrote a column in September 1994 foreshadowing that John Howard would return to the leadership, and I was the only person in the country who said it. And Tony Abbott always said, ‘I reckon you belled the cat.’ It just gave it a legitimacy – and he thought it was a seminal column.’’

Cate McGregor, the woman in uniform and lipstick, suddenly gears down her voice to a faultless impression of Abbott that turns the head of the gentleman at a nearby table.

‘‘And so he said to me – y’know Tony’s got that mad axe-murderer laugh: ‘Heh-heh, mate, heh-heh-hah, for your services to the Liberal Party, mate, with the liquidation of – heh-heh-heh – John Hewson and to ensuring the return of truth and light to the leadership, mate – hah-hah – for all this, as we say in Rome, mate: You’re absolved!’’’

McGregor was not so readily absolved for the aerial bombing of Labor. ALP powerbroker Laurie Brereton had told McGregor: ‘‘We’re gonna rub you out.’’ ‘‘I went on Four Corners and looked down the barrel of the camera and said Brereton was a dingo. Bring it on! I said he’ll be too old before he’s good enough. He’s never been in a fight ... And I said, like the rest of the NSW Right, they’re all hard men in the way that a teenage gang kicking a wino are hard men. And I said there’s not one of ’em I wouldn’t mind going down a dark alley way with – unless Tom Domican [a truly hard Labor man] was in tow with them. I was insane, crazy-brave.’’

McGregor realises now that Malcolm’s macho aggression was masking something much deeper, much more disturbing. ‘‘A death wish was driving me.’’

She refers to a study of 150 trans women over 30 years. ‘‘They were massively over-represented in alpha-male professions, risk-taking, hyper-masculine pursuits. Probably the three most obvious trans military women in the world are myself, Ayla Holdom, who was a jet fighter pilot with the Royal Air Force and now flies helicopters, and Kristin Beck, the former US navy seal. She was in the team [as Christopher Beck] that busted Osama Bin Laden.’’

McGregor, the woman, can declare now: ‘‘It’s amazing the bliss and ease in my own skin.’’

On Wednesday night she and Chaz Bono – formerly Chastity, Sonny and Cher’s only child – will feature at the Seymour Centre in the Gay and Lesbian Mardi Gras event ‘‘Queer Thinking: Gender Trailblazers’’. On Friday night McGregor will join a feminist forum, ‘‘Women Say Something’’, at Sydney Town Hall. She has arrived as a woman. But only two years ago she was a mess: depressed, battling an eating disorder and resisting the persistent voice in her head telling her she could no longer live as Malcolm.

‘‘It was chaos. I thought, ‘Am I going mad? There’s no upside to becoming a woman. I’ll be a laughing stock. I’m going to hurt the person I love most in the world. I’ll lose my marriage. I’ll lose my job, my career, my house.’ I probably didn’t get more than two hours sleep on any given night for six months.’’

Malcolm McGregor was born in 1956, one of four children in a devoutly Catholic family in Toowoomba in southern Queensland. He recalls a life of Arcadian simplicity, the long summers of backyard cricket, two kids to a bedroom, the wood-burning stove. ‘‘We were very religious.

One sister became a nun.’’Malcolm was a small boy when his father, a World War II veteran, died in 1964. Malcolm was in second grade, about seven, when he first became curious about his sexuality.

‘‘I physically tried on my mother’s clothes when I was eight, going on nine. I remember thinking I just wanted to experience it ... to see how it felt to be a girl. And I remember it felt quite right.’’

Young Malcolm’s mother caught him, and to her it was just wrong. ‘‘She really flew at me. So I just didn’t do it again, until four years later. I had broken my ribs and I had the house to myself, so I experimented again. But there was some tell-tale sign. I left a lipstick stain or something. My mum was just extreme in her response.

"I’d had a really rigid upbringing. And I was a real goody two-shoes: academically strong, good at sport.’’ Malcolm was vice-captain at his Christian Brothers high school. ‘‘And then straight into Duntroon, which in the 1970 was run like a moderately enlightened Cistercian community from the medieval era.’’He had never considered any other career but the army. ‘‘I’m sure it was a kind of maladroit attempt to win my father’s approval or to connect with him in some way. And I was probably trying to quell my disquiet about my gender, as well.’’

Out of Duntroon, McGregor’s delayed political awakening came in a rush from the left. ‘‘I channelled a lot of intensity into external causes for a long time because I didn’t know what was going on inside.’’

He also took to the drink with a vengeance. In 1985, a counsellor diagnosed McGregor as transgender, but Malcolm repressed those feelings for the next 26 years. He would quit drinking in 1990 and get on with his life as a man. He had been with his wife, Tritia – ‘‘the love of my life’’ – for about 15 years when, in 2010, he went into therapy for what he assumed was a typical male mid-life crisis: lethargy, depression, ‘‘loss of animation and volition’’.

Always fit, his body weight hadn’t deviated in 25 years, but suddenly he gained 16 kilograms and peaked at 85kg. Then followed an eating disorder and McGregor’s weight plummeted to 63kg.On the last Sunday in October, 2011, he was rocked by a story in The Sun-Herald about the former champion surfer Peter Drouyn who, after reassignment surgery in 2008, was living happily as Westerly Windina. ‘‘It really was the detonator event,’’ says McGregor.

Malcolm was working on a book, An Indian Summer of Cricket, but ‘‘I literally couldn’t expel the thought that I was really female. It was like a fly wheel inside my psyche, and it just seemed to keep whirring.’’

On the last full day of the Adelaide Test in January 2012, McGregor was in the grandstand. ‘‘I’d been awarded the Order of Australia the day before,’’ he says.

‘‘They’d announced it at the Adelaide Oval. Ricky Ponting and I were both in the same list. And I’m sitting in the grandstand thinking I’d rather be dead.’’

McGregor broke down with an anxiety attack. It was the Indian team doctor, as she recalls, who came to his aid. By mid-year McGregor had made the final decision to transition. Her sole regret is that it ended her marriage.

‘‘I never entered that marriage with the slightest doubt that I would get old with her, the woman I love. But she got through her grief and anger and sense of betrayal in the most extraordinarily courageous and dignified way. And we remain really, really close. She now sees me as a woman, which is incredibly affirming.’’

So does Lieutenant General David Morrison, McGregor’s boss. He refused her offer to resign and she is among 15 transgender people in the defence forces.

McGregor left it to the last chapter of her book, written as Malcolm, to tell readers she would be a woman by the time they were reading it. Tony Abbott wrote a review in which he lauded her courage.

McGregor voted for Abbott’s government, though some differences remain between them. But she says it would be ‘‘churlish and incredibly disloyal’’ to attack him publicly on matters such as gay marriage ‘‘when he’s been so supportive of me’’.

‘‘He’s done it at some risk to his core constituency. Cory Bernardi would tar and feather me, I suspect. There’s a large slab of conservative opinion that would think I’m utterly repulsive. Tony’s support for me, overtly, comes at some cost [to him], while it will get him cheap applause from people who will never vote for him. He’s made a sacrifice in the name of friendship, and if my sacrifice is not to run around crusading against him, then I think it’s a fair bargain.’’